For each reaction in question 20, sketch a reaction coordinate energy diagram indicating the starting materials, transition states and any intermediates, if present, in the reaction

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter26: Lipids
Section26.6: Fat-soluble Vitamins
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For each reaction in question 20, sketch a reaction coordinate energy diagram indicating the starting materials, transition states and any intermediates, if present, in the reaction. Don't worry about the absolute energy of starting materials and products but you can assume that the product is more stable than the starting materials. 

20. When the acetate of (S)-2-pentanol is heated in water which contains ammonium
chloride, a racemic mixture of (S)- and (R)-2-chloropentane is produced (reaction
A). When the same reaction is carried out in dimethylformamide (DMF) as the
solvent, only the (R) product is obtained (reaction B). Answer the following about
these reactions:
NH,CI, H,O
A
heat
50:50
NHẠCI, DMF
B
only product
heat
a. By what mechanism are these reactions proceeding? (circle the correct
mechanism)
Reaction A:
SN1
Sx2
El
E2
Reaction B:
Syl
Sx2
E1
E2
b. Why did reaction A give a mixture of products? Be sure to use and orbital
argument to support your answer.
Transcribed Image Text:20. When the acetate of (S)-2-pentanol is heated in water which contains ammonium chloride, a racemic mixture of (S)- and (R)-2-chloropentane is produced (reaction A). When the same reaction is carried out in dimethylformamide (DMF) as the solvent, only the (R) product is obtained (reaction B). Answer the following about these reactions: NH,CI, H,O A heat 50:50 NHẠCI, DMF B only product heat a. By what mechanism are these reactions proceeding? (circle the correct mechanism) Reaction A: SN1 Sx2 El E2 Reaction B: Syl Sx2 E1 E2 b. Why did reaction A give a mixture of products? Be sure to use and orbital argument to support your answer.
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